Cesium carbonate → N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide

Participants

Reaction Steps

A solution of 2-(4-chlorophenylsulfonamido)bicyclo[2.2.1]heptan-7-ol (604 mg, 2.0 mmol), cesium carbonate (1.30 g, 4.0 mmol), and 4-(bromomethyl)benzonitrile (471 mg, 2.4 mmol) was stirred in 10 mL dimethylformamide for 1 h. The crude reaction product was treated with additional cesium carbonate (261 mg, 0.8 mmol) and 4-(bromomethyl)benzonitrile (94 mg, 0.5 mmol) to complete the reaction. The reaction was partitioned between 50 mL ethyl acetate and 50 mL 0.1 M HCl, concentrated and purified by flash chromatography on 120 g silica gel with 30 to 50% ethyl acetate in hexane to yield N-(4-cyanobenzyl)-N-(7-hydroxybicyclo[2.2.1]heptan-2-yl)-4-chlorobenzenesulfonamide (412 mg, 49%). 1H NMR (400 MHz, CDCl3) δ ppm 7.70-7.77 (2H, m), 7.59 (2H, d, J=8.56 Hz), 7.44-7.50 (4H, m), 4.81 (2H, dd, J=39.53, 17.88 Hz), 4.06 (1H, t, J=7.81 Hz), 3.84 (1H, br. s.), 1.91 (1H, br. s.), 1.75-1.82 (2 Hon), 1.43-1.66 (3H, m), 1.07-1.17 (2H, m). LC/MS R.T.=1.97 min; [M+H]+=417.15.

Provenance & Evidence